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Set up to Fail

“Innovation and failure go hand in hand, we make a lot of mistakes and we fail a lot. We don’t believe you can separate failure from innovation. That’s absolutely fine, because innovations that succeed pay for an awful lot of ideas.”
~ Jeff Bezos

No discussion of goals would be complete without a discussion of missing the mark, aka failure. We often think of being set up to

fail as a negative. I suppose it is. No one wants to start a mission knowing that it’s really a suicide mission.

But being set up to fail can take on a different connotation in the sense that you can be given room to fail safely. We never want to fail for failure’s sake. It is wise to study, plan, prepare, and work smartly. However, when a company (or a family, or a church, or a charity, etc.) can create an environment where people know their failures will be celebrated as learning lessons, they are more willing to take calculated risks. They are more eager to experiment. And when people try new things, they often have that “Eureka” moment when they discover something that makes everyone’s work more effective and efficient.

In the end, if you try and fail, you have essentially succeeded because every try is filled with information. Your mission, however, is to succeed. The only downside of failure is that it often paralyzes someone who might have otherwise succeeded. Their conversation changes from one of affirmation to one of lamentations. Over time, they bond with their failure stories and tell them over and over like war stories. Failure is incomplete until and unless you quit. If you quit, failure becomes final. If you forge ahead, failure becomes a rung on the ladder to the top.

You may fail many times. That’s okay. There is no quota for failure. Each time you fail, you must remind yourself that there was some critical element you didn’t have that was needed for success. With reflection, you can pound out that chink in your armor, suit up, and go again. If you have failed often, congratulations! You had a lot to learn, and you learned it if you took the time to ask how and why the failure occurred. Life offers a free education about what works and what doesn’t. After the failure, climbing to where you were is easier, and you must stretch to reach the next rung.

“Success is how high you bounce when you hit bottom.”
~ General S. Patton, US Army

It does not matter that you tried unless you commit to finishing. This is a ride-or-die, never-quit, success-or-bust commitment to run all the way to the end and see what you are truly capable of. I can guarantee you that there is more inside you than you know.

“There’s likely a place in paradise for people who tried hard, but what really matters is succeeding. If that requires you to change, that’s your mission.”
~ General Stanley McChrystal, US Army Retired

What’s important about a company that lives on Day 1 is that you find that it is all right to fail. Amazon knows that failure teaches valuable lessons. It’s a lesson that Amazon has learned over and over as it has gone from a start-up e-commerce book company to one of the world’s largest and most innovative companies. Food, movies, kitchenware, car parts, and a seemingly infinite number of other items, including books, can be found at Amazon. Tomorrow is another day. Institutional blindness to failure was extremely hard to grasp, considering that failure in the Army could often mean lives, but Amazon sees it as an opportunity to grow and focuses on the why at short meetings called Syncs, where managers dissect and analyze how to get better. The lesson is that success doesn’t happen to the perfect or the one who doesn’t make mistakes; it is borne out of risking and learning from failure, which is an absolute part of the process.

All of that said, remember that one of Amazon’s leadership principles is that leaders Are Right, A lot. The company expects that, as a result of your intelligence and experience, you have already made a lot of mistakes and have gained the judgment, insight, and foresight to know many things that will and won’t work. In military terms, you have been battle-tested. You cannot simply expect to make error after error, throwing things against the wall to see if they stick.

It’s a bit of a balancing act where you have to allow yourself the freedom to try something new and different while also exercising the judgment necessary to know if it has a good chance of working. My advice is to wargame your idea in your head first. Don’t just think about all the ways it will work; consider the potential pitfalls as well. What are the weak areas of your plan? What parts of the company will it impact? You can fix a problem in one part of a behemoth like Amazon and cause a problem in another part. You are the cream of the crop, so Amazon will expect you to think through the eventualities as best you can. Then, if you fail, see if the plan can be revised or if it needs to be discarded.

It was empowering to know that getting better is also essential to succeeding at Amazon. Over a long military career, I learned that there are both reasons and results. We have all found ourselves in a position where we have had to explain why we did not accomplish a task or meet a metric. This introspective deep dive into the why is a daily occurrence at Amazon and is meant to help not only the organization but all teams achieve the results outlined for the day and, more importantly, be successful tomorrow.


Leadership is solving problems. The day soldiers stop bringing you their problems is the day you have stopped leading them.
They have either lost confidence that you can help or concluded you do not care. Either case is a failure of leadership.
~ Colin Powell, former Chairman of the Joint Chiefs of Staff, Secretary of State, Author, and Mentor

I couldn’t be more happy to join this company after my military service. I feel like I am still contributing at a very high level. Life after the uniform is not so bad.

Continued connection with friends, increased communication with family, hobbies, and secondary activities have all contributed to my transitional success; in addition, I would highlight the development of deep and meaningful relationships with workmates who have also energized me to the level of my former military comradeships. Notice that I have not listed anything about the job, work-life balance, commute, or demanding bosses. Sure, all of those things play a part as well, but ultimately, I know that I would not have a successful second career without all of the soft attributes I initially highlighted.

There’s a lot in transition that Amazon has given me, but one of the most important things has been the establishment of connections with those who have either needed or wanted my help. To my surprise, I have continued to mentor leaders on a larger scale than even when I was in the military. Part of that is because of the blog and the reach I have established through its readership, but a large portion of the relationships I have are through referrals from fellow leaders from within Amazon as well as former military connections. So, no matter what my current work position is, I am still able to share my experience and continue to grow as a leader.

Hiring Our Heroes has been one of the joys of my life. Amazon partners with dozens of companies to host events that hire retired military personnel. Many receive job offers on the spot.

Early on, I recognized that if I only focused on what I was doing, it would not sustain me over a long period of time or even a short, successful career at Amazon. I developed this win-in-the-margins mentality and gave myself the permission to focus on things other than work.

Too many folks retire after a long military or civilian career and think that they will be satisfied sitting at home watching TV or working in the yard – maybe, but probably not. Far too many of us lack the direction to ensure long-term relevance. For some, that relevance comes in the form of a job or second career; my contention is that your career will be bolstered by those other things that you do in conjunction with meaningful work. In fact, the work does not even have to be meaningful if you stack enough of the other goodness.

I believe that finding this purpose and winning in the margins is the most important reason I have succeeded in my career at Amazon. Don’t get me wrong: I have had some extremely trying and tough days; I have also had experiences that have challenged my understanding of myself as a leader, but my second career outlook has always mitigated these challenges.

A call to my Mom, lunch with a friend, or the requirement to meet with someone that I am mentoring provides an instant reset and mandates a clear head and positive attitude. In the end, no working issue survives first contact with Mom or the blunt forthrightness of a German wife. With this type of support, maybe my satisfaction with my second career at Amazon was preordained.


Lee Flemming is a retired Army Colonel currently working at the Austin 2 (AUS2) Fulfillment Center in Pflugerville, Texas, as the General Manager for the site. He is a successful graduate of the Amazon Military Pathways Program. He is a 28-year Army Veteran with extensive operations and management experience.

In the Army, he was an Infantry officer who served in Bosnia and Kosovo and is a veteran of the Iraq War. He made his mark on history as the first African American Installation commander in NATO’s 74 years of existence after leading the Installation and Base Support Group of the Supreme Headquarters Allied Powers Europe (SHAPE).

Colonel Flemming is a graduate of the University of Houston and holds a Master’s of Arts degree in Public Administration, a Master’s of Military Arts and Sciences degree from the US Army Command and General Staff College, and a Master’s Degree in National Security from the National Defense University. He is also the 1986 recipient of the Legion of Valor Bronze Cross for Achievement. Flemming’s military education includes the Infantry Officer’s Basic and Advanced Courses, the Command and General Staff College, a War College Fellowship.

The United States Army Airborne and Air Assault Schools, the Bradley Leader’s Course, and the United States Army Ranger School.

His awards and decorations include:

• Defense Superior Service Medal

• Legion of Merit

• Bronze Star (1 OLC)

• Defense Meritorious Service Medal

• Meritorious Service Medal (4 OLC)

• Army Commendation Medal (4 OLC)

• Army Achievement Medal (1 OLC)

• Global War on Terror Service Medal

• Armed Forces Expeditionary Medal

• Iraq Campaign Medal

• Kosovo Campaign Medal

• NATO Medal

• National Defense Service Medal

• Army Service Ribbon

• Combat Infantryman Badge

• Expert Infantryman Badge

• Parachutist Badge

• Air Assault Badge

• Ranger Tab

His blog includes regular installments meant to inform and educate Service Members and the public about transitioning into employment at Amazon and other second careers.

Flemming Battalion Command Circa 2011

Lee and Michaela Flemming

Change of Command

Birthdays in the Army

Deep Run in the World Series of Poker

Dad and Marine Andrew Flemming

Promotion with Mom (Velma Lewis Moss), Michelle, and LTG R. Twitty

Shape Command Team, Cliff Neil

Sisters Katherine Guillory and Beverly Dyer

Retirement, Michelle, Daughter Shareice, and Niece Diamond

1 Year Amazon Anniversary

Amazon Experience


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